Chiral Phosphoric Acid-Catalyzed Enantioselective Dearomative Electrophilic Hydrazination: Access to Chiral Aza-Quaternary Carbon Indolenines

Direct enantioselective synthesis of chiral aza-quaternary carbon indolenines through the dearomative electrophilic hydrazination of 2,3-disubstituted indoles has been achieved. This catalytic asymmetric strategy leads to the efficient construction of a series of enantioenriched aza-quaternary carbon indolenines in high yields and excellent stereoselectivities. The synthetic practicality of this reaction has been demonstrated by the enantioselective modification and derivatization of drug molecules. In-situ infrared and density functional theory calculations suggest that our catalytic system could overcome the background reaction to achieve effective enantioselective dearomatization.

Automated summary

In this study, the direct enantioselective synthesis of chiral aza-quaternary carbon indolenines was achieved through catalytic asymmetric strategy, and its potential in drug molecule modification was demonstrated.